Review
Chemistry, Multidisciplinary
Jiarong Shi, Lianggui Li, Yang Li
Summary: Arynes are highly active organic intermediates used in the rapid synthesis of substituted arenes, with o-silylaryl triflates being the most frequently employed precursors. The resurgence in aryne chemistry over the past 20 years is largely attributed to the widespread use of Kobayashi's method, which involves fluoride-induced removal of the TMS group with concomitant departure of its ortho OTf group. This review provides an overview of the history, achievements, and applications of Kobayashi's method in the synthesis of natural products, bioactive molecules, and polycyclic aromatic hydrocarbons.
Article
Chemistry, Physical
Chau Ming So, On Ying Yuen, Shan Shan Ng, Zicong Chen
Summary: This study presents a general chemoselective Suzuki-Miyaura coupling using a Pd/L33 catalyst, showing efficient coupling of polyhalogenated aryl triflates by controlling reactivity order and key factors, achieving high yields and chemoselectivity with low Pd catalyst loading.
Article
Chemistry, Organic
Feiyan Yang, Chuan Wang
Summary: In this study, we employ polycyclic aryl-activated alkyl ammonium triflates as the electrophilic aryl-activated alkylating agent in the nickel-catalyzed hydroxyl- or sulfonamide-directed cross-electrophile coupling reaction with phenyl benzoates, resulting in the synthesis of diverse aryl ketones under mild conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Bing-Yu Li, Lauren Voets, Ruben Van Lommel, Fien Hoppenbrouwers, Mercedes Alonso, Steven H. L. Verhelst, Wim M. De Borggraeve, Joachim Demaerel
Summary: Sulfur(VI) Fluoride Exchange (SuFEx) chemistry has emerged as a next-generation click reaction for assembling functional molecules quickly and modularly. This study demonstrated the generation of trifluoromethanesulfonyl fluoride (CF3SO2F) gas in a two chamber system, and its use in the efficient synthesis of triflates and triflamides, with potential applications in peptide modification or coupling reactions. Additionally, redesigning the S-VI-F connector to furnish triflimidoyl fluorides as SuFEx electrophiles allowed for the synthesis of rarely reported triflimidate esters, with H2O identified as a key factor in achieving chemoselective trifluoromethanesulfonation of phenols versus amine groups.
Article
Chemistry, Multidisciplinary
Fariba Jafari, Arash Ghorbani-Choghamarani, Neda Hasanzadeh
Summary: Boehmite nanoparticles were synthesized in aqueous solution by combining Al(NO3)3·9H2O and NaOH, which were then converted to Pd-Gu@BOEH nanocatalyst for chemoselective C-C bond formation reactions. The catalyst and products were characterized, and the recycled catalyst exhibited good stability during reaction processes.
RESEARCH ON CHEMICAL INTERMEDIATES
(2021)
Article
Chemistry, Applied
Mahdi Keyhaniyan, Amir Khojastehnezhad, Hossein Eshghi, Ali Shiri
Summary: An efficient procedure was reported to prepare Fe3O4@SiO2 magnetic nanoparticles (MNPs) with immobilized nickel NPs for the synthesis of biaryl derivatives via the Suzuki-Miyaura cross-coupling reaction. The catalyst showed high activity and could be recovered and reused with no loss of activity over multiple runs.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Tomas Chvojka, Athanasios Markos, Svatava Voltrova, Radek Pohl, Petr Beier
Summary: The stereoselective Suzuki-Miyaura cross-coupling of (Z)-beta-enamido triflates is demonstrated, showing different retention or inversion of configuration in the synthesis of beta,beta-diaryl-substituted enamides depending on the ligand in the palladium catalyst. This method provides access to both isomers of the target enamides from (Z)-beta-enamido triflates.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jin Zhang, Pei Zhang, Lei Shao, Ruihong Wang, Yangmin Ma, Michal Szostak
Summary: A highly chemoselective, solvent-free mechanochemical strategy for the cross-coupling of amides by N-C bond activation has been reported. The method shows excellent selectivity, functional group tolerance, and can be applied for late-stage functionalization of complex molecules. This extends the repertoire of N-C bond interconversions to solid-state environmentally friendly mechanochemical methods.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Inorganic & Nuclear
Mehran Farhang, Ali Reza Akbarzadeh, Mahboubeh Rabbani, Amir Mohammad Ghadiri
Summary: Carbon-carbon coupling is an important reaction that has implications in chemical, academic, and industrial fields. The Suzuki-Miyaura coupling, a cross-coupling reaction, is particularly significant in producing biaryls that possess pharmaceutical properties. This review categorizes the pharmaceutical biaryl products of the Suzuki reaction into various groups, highlighting their potential applications in drug development. Additionally, the use of continuous flow processes in pharmaceutical production is explored, emphasizing its advantages over traditional batch or semi-batch methods.
Article
Polymer Science
Yuehui Yuan, Zhiyi Song, Masayoshi Bando, Tamaki Nakano
Summary: By catalyzing benzene amine and ketone composites with zinc vapor and 2,2’-biphenyl doping, benzylamine porous organic crystals are formed, which exhibit excellent performance in gas adsorption and selective dye adsorption.
Article
Materials Science, Paper & Wood
Pouya Ghamari Kargar, Milad Nayebi, Zahra Parhizi, Rajender S. Varma
Summary: An eco-friendly approach was used to generate Ni nanoparticles on a magnetized cellulose biopolymer, resulting in a core-shell type nanocomposite (Fe3O4@CNF@Ni). The nanocomposite was characterized using various advanced techniques and its catalytic performance was evaluated in the synthesis of biaryl derivatives. The results showed that the nanocomposite exhibited high stability and catalytic efficiency.
Article
Chemistry, Multidisciplinary
Zicong Chen, Changxue Gu, On Ying Yuen, Chau Ming So
Summary: This study described a selective palladium-catalyzed direct α-arylation reaction using chloroaryl triflates and carbonyl compounds. The reaction exhibited excellent chemoselectivity towards the Ar-Cl bond with a broad substrate scope and high product yields. The electronic and steric effects of the -PR2 group and C2-alkyl group were found to be crucial for the reactivity and selectivity of the α-arylation reaction. This chemodivergent approach was also successfully applied in the synthesis of flurbiprofen and its derivatives (-OMe and -F).
Article
Chemistry, Multidisciplinary
Weixu Lu, Xiaoqiang Yu, Ming Bao
Summary: In this paper, a group of copper-based ternary deep eutectic solvents (Cu-DESs) were synthesized and applied in Glaser-type homo- and cross-coupling of terminal alkynes. These reactions occurred under exogenous-ligand-free, base-free, and additive-free conditions, providing satisfactory to excellent yields (up to 99%) under mild conditions. The Cu-DESs can be recycled eight times, with water being the only by-product, complying fully with the principles of green chemistry.
Article
Multidisciplinary Sciences
Lara E. Zetzsche, Jessica A. Yazarians, Suman Chakrabarty, Meagan E. Hinze, Lauren A. M. Murray, April L. Lukowski, Leo A. Joyce, Alison R. H. Narayan
Summary: This study demonstrates the use of cytochrome P450 enzymes for biocatalytic cross-coupling reactions, enabling the formation of sterically hindered biaryl bonds through oxidative C-C bond formation. By engineering the substrate and atroposelectivity of the P450 enzyme, a highly efficient and selective process has been developed.
Review
Chemistry, Physical
Brijesh S. Kadu
Summary: Palladium has been widely used in the Suzuki-Miyaura cross coupling reaction for over 30 years, but it comes with drawbacks such as high cost, tedious work-ups, product contamination, and metal leaching. In recent years, other metals like Ni, Cu, Co, Fe, Rh, and Ru have attracted attention for their potential in SMCR, allowing for the synthesis of industrially important compounds with various functional groups. This review discusses recent advancements in catalysis related to SMCR, providing valuable insights for researchers in designing synthetic protocols for pharmacophores and drug molecules.
CATALYSIS SCIENCE & TECHNOLOGY
(2021)
Article
Chemistry, Organic
Allan F. C. Rossini, Ana Carolina A. Muraca, Gleison A. Casagrande, Cristiano Raminelli
JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Multidisciplinary
Eric F. S. dos Santos, Nathalia M. Cury, Tainara A. do Nascimento, Cristiano Raminelli, Gleison A. Casagrande, Claudio M. P. Pereira, Euclesio Simionatto, Jose A. Yunes, Lucas Pizzuti
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY
(2017)
Article
Chemistry, Multidisciplinary
Carlise Frota, Allan F. C. Rossini, Gleison A. Casagrande, Lucas Pizzuti, Cristiano Raminelli
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY
(2017)
Article
Chemistry, Organic
Ana Carolina A. Muraca, Givago P. Perecim, Alessandro Rodrigues, Cristiano Raminelli
SYNTHESIS-STUTTGART
(2017)
Article
Polymer Science
Rebeca Rocha Rodrigues, Cristiano Raminelli, Laura Oliveira Peres
EUROPEAN POLYMER JOURNAL
(2018)
Article
Chemistry, Medicinal
Etyene J. G. Silva, Adriana Bezerra-Souza, Luiz F. D. Passero, Marcia D. Laurenti, Glaucio M. Ferreira, Drielli G. Fujii, Gustavo H. G. Trossini, Cristiano Raminelli
FUTURE MEDICINAL CHEMISTRY
(2018)
Article
Chemistry, Organic
Bianca K. Correa, Tamiris R. C. Silva, Cristiano Raminelli
TETRAHEDRON LETTERS
(2018)
Article
Electrochemistry
Thays Souza Lima, Mauro A. La-Scalea, Cristiano Raminelli, Fabio R. Simoes, Edison Franco, Gabriela Dias da Silva, Michele Aparecida Salvador, Paula Homem-de-Mello, Hueder P. M. de Oliveira, Lucia Codognoto
JOURNAL OF SOLID STATE ELECTROCHEMISTRY
(2019)
Article
Oncology
Dorival Mendes Rodrigues-Junior, Nicolie Melanie de Almeida Pontes, Gabriela Estrela de Albuquerque, Viviane Carlin, Givago Prado Perecim, Cristiano Raminelli, Andre Luiz Vettore
INVESTIGATIONAL NEW DRUGS
(2020)
Article
Chemistry, Multidisciplinary
Ana Carolina A. Muraca, Cristiano Raminelli
Article
Chemistry, Organic
Givago P. Perecim, Victor M. Deflon, Gabriel R. Martins, Leandro M. C. Pinto, Gleison A. Casagrande, Diogo Oliveira-Silva, Cristiano Raminelli
Article
Chemistry, Multidisciplinary
Tamiris R. C. Silva, Vinicius V. Souza, Cristiano Raminelli
Summary: In this study, we investigated the reaction of several substituted oxazoles with o-(trimethylsilyl)aryl triflates promoted by potassium fluoride and 18-crown-6-ether. We obtained functionalized isoquinoline compounds in moderate to good yields at room temperature through a [4+2] cycloaddition-ring-opening reaction pathway, followed by acidic workup. Alternatively, bicyclic ethers were produced in reasonable yields at 60 degrees C through a sequence of [4+2] cycloaddition, retro-Diels-Alder, and [4+2] cycloaddition reactions.
Article
Chemistry, Organic
Beatriz C. O. Rocha, Givago P. Perecim, Cristiano Raminelli
Article
Chemistry, Multidisciplinary
Matheus A. Meirelles, Alex H. Jeller, Irlon M. Ferreira, Cristiano Raminelli, Raquel S. Faria, Elisangela de Paula Silveira-Lacerda, Andre L. M. Porto
CURRENT MICROWAVE CHEMISTRY
(2017)
